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US 5,495,021 AGranted
Benzo[f]quinolinones
AssigneeEli Lilly and Company
InventorsJames E. Audia, David E. Lawhorn, Leland O. Weigel
Life of this patent
Estimating the term…
Abstract
This invention relates to hexa- and octahydrobenzo[f]quinolin-3-ones, pharmaceutical formulations containing those compounds and methods of their use as steroid 5.alpha.-reductase inhibitors.
Claims2
A process of resolving racemates of the 4a,10b-transenantiomers of those compounds having the Formula ##STR22## where R is hydrogen or C.sub.1 -C.sub.4 alkyl;
- Z and Z.sup.1 are independently selected from hydrogen and C.sub.1 -C.sub.4 alkyl;
- Y is hydrogen;
- R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are all hydrogen;
- n is 1 or 2;
- and
- X is hydrogen, halogen, NO.sub.2, CF.sub.3, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.4 alkoxy, amino, C.sub.1 -C.sub.4 alkylamino, C.sub.1 -C.sub.4 dialkylamino, mercapto, or C.sub.1 -C.sub.6 alkylthio;
- into their component optical isomers comprising essentially the steps of:
- (a) contacting a methanol solution of said racemate with a strong acid to afford a 1-(2-methoxycarbonylethyl)-2-(amino)-1,2,3,4-tetrahydronaphthalene;
- (b) contacting said tetrahydronaphthalene from (a) with a methanol solution of an optically active di-p-toluoyltartaric acid to afford a corresponding tetrahydronaphthalene salt;
- and
- (c) treating said salt from (b) with a base to obtain a free amine having substantially one optically active isomer;
- (d) heating said free amine from (c) at a temperature from about 35.degree. C. to about 120.degree. C. to recyclize and afford the desired octahydrobenzo[f]quinolinone.
9 more elements
A salt of di-p-toluoyl-(D) or (L)-tartaric acid and a trans isomer of a compound having the formula ##STR23## where R is hydrogen or C.sub.1 -C.sub.4 alkyl;
- Z and Z.sup.1 are independently selected from hydrogen and C.sub.1 -C.sub.4 alkyl;
- n is 1 or 2;
- and
- X is hydrogen, halogen, NO.sub.2, CF.sub.3, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.4 alkoxy, amino, C.sub.1 -C.sub.4 alkylamino, C.sub.1 -C.sub.4 dialkylamino, mercapto or C.sub.1 -C.sub.6 alkylthio.
1 more element
Dependencies are inferred from the claim text.